3116-76-5

Basic information

• Product Name: Dicloxacillin
• Synonyms: )-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3///;4-thia-1-azabicyclo(3.2.0)heptane-2-carboxyl///;4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(((3-(2,6-dichlorophenyl;6-(3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanicacid[qr;6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-6-(3-(;brl1702;dicloxacilin;dicloxacycline
• CAS NO: 3116-76-5
• Molecular Formula: C₁₉H₁₇Cl₂N₃O₅S
• Molecular Weight: 470.33
• EINECS: 221-488-3
• Mol File: 3116-76-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 218 °C (decomp)
• Boiling Point: 692.4 °C at 760 mmHg
• Flash Point: 372.5 °C
• Appearance: /
• Density: 1.62 g/cm³
• Vapor Pressure: 3.98E-20mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: 2-8°C
• PKA: pKa 2.76(H2O t=37 I=0.15 (KCl)) (Uncertain)
• Water Solubility: 3.63 mg/L
• CAS DataBase Reference: Dicloxacillin(CAS DataBase Reference)
• NIST Chemistry Reference: Dicloxacillin(3116-76-5)
• EPA Substance Registry System: Dicloxacillin(3116-76-5)

Safety Data

• Hazardous Substances Data: 3116-76-5(Hazardous Substances Data)

Usage

Description

Chemically this is 3(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl penicillin. It differs from cloxacillin by having two chloride ions attached to the phenyl group. It comes as oral capsules of 250 and 500 mg, and in an injectable formulation of 500 mg and 1 g.

Uses

Antibacterial.

Definition

ChEBI: A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]formyl group.

Therapeutic Function

Antibacterial

Antimicrobial activity

It is very highly bound to serum protein, and its activity in the presence of human serum in vitro is depressed to a greater extent than that of other isoxazolylpenicillins.

Pharmacokinetics

Oral absorption: c. 50% Cmax , 250 mg oral: 9 mg/L after 1 h 500 mg intramuscular: 14–16 mg/L after 0.5–1 h Plasma half-life: 0.5 h Plasma protein binding: 95–97% Absorption Absorption in the very young is poor and unpredictable. Metabolism and excretion Dicloxacillin is partly metabolized in the liver and about 10% of the circulating drug is in the form of metabolites. Some 50–70% of a dose is excreted in the urine, about 20% as metabolites. It is eliminated both in the glomerular filtrate and by tubular secretion, and plasma concentrations are raised by probenecid. Parent drug and increased proportions of metabolites accumulate in renal failure. Elimination is increased through enhanced tubular secretion in patients with cystic fibrosis.

Pharmacology

In terms of mechanism of action, antibacterial spectrum, and indications for use, it is essentially no different than oxacillin and cloxacillin. Synonyms of this drug are diclocil, novapen, diclex, and others. The following type of semisynthetic penicillins that should be considered are those in which amino acids, mainly α-aminophenylacetic or p-oxy-α-amino-phenylacetic acids, act as the acyl radical (ampicillin, amoxacillin). The antimicrobial spectrum of aminopenicillins is similar to penicillin G, with the exception that they also act on a number of Gram-negative microorganisms. Both aminopenicillins are destroyed by staphylococcus penicillinase.

Side effects

Phlebitis is common after intravenous injection. Its toxicity is otherwise similar to that of other penicillins. Clinical uses are those of the group 3 penicillins.

InChI:InChI=1/C19H17Cl2N3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1

Synthetic route

dicloxacillin (3116-76-5) + water (7732-18-5) + copper diacetate (142-71-2) → Cu(C19H16N3O5SCl2)(H2O)(OCOCH3)

Conditions	Yield
In ethanol; water aq. soln. of Cu salt and ligand (molar ratio 1:1) in water-EtOH refluxedfor 1 h; concd.; filtered; ppt. washed with hot H2O-EtOH; dried in vac. over anhyd. CaCl2; elem. anal.;	80%

dicloxacillin (3116-76-5) + water (7732-18-5) + iron(II) chloride → Fe(C19H16N3O5SCl2)Cl(H2O)3*2H2O

Conditions	Yield
In ethanol; water aq. soln. of FeCl2 and ligand (molar ratio 1:1) in water-EtOH refluxed for 1 h; concd.; filtered; ppt. washed with hot H2O-EtOH; dried in vac. over anhyd. CaCl2; elem. anal.;	80%

dicloxacillin (3116-76-5) + water (7732-18-5) + cobalt(II) chloride (7646-79-9) → Co(C19H16N3O5SCl2)Cl(H2O)3*2.5H2O

Conditions	Yield
In ethanol; water aq. soln. of CoCl2 and ligand (molar ratio 1:1) in water-EtOH refluxed for 1 h; concd.; filtered; ppt. washed with hot H2O-EtOH; dried in vac. over anhyd. CaCl2; elem. anal.;	78%

dicloxacillin (3116-76-5) + water (7732-18-5) + iron(III) chloride (7705-08-0) → Fe(C19H16N3O5SCl2)Cl2(H2O)2*2H2O

Conditions	Yield
In ethanol; water aq. soln. of FeCl3 and ligand (molar ratio 1:1) in water-EtOH refluxed for 1 h; concd.; filtered; ppt. washed with hot H2O-EtOH; dried in vac. over anhyd. CaCl2; elem. anal.;	75%

dicloxacillin (3116-76-5) + water (7732-18-5) + nickel dichloride → Ni(C19H16N3O5SCl2)Cl(H2O)3*2.5H2O

Conditions	Yield
In ethanol; water aq. soln. of NiCl2 and ligand (molar ratio 1:1) in water-EtOH refluxed for 1 h; concd.; filtered; ppt. washed with hot H2O-EtOH; dried in vac. over anhyd. CaCl2; elem. anal.;	75%

dicloxacillin (3116-76-5) → Dicloxacillin S-sulphoxide (36231-31-9)

Conditions	Yield
With sodium periodate or Dicloxacillin sodium salt;

dicloxacillin (3116-76-5) → phenoxymethylpenicillin sulfoxide (4888-90-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaIO4 / or Dicloxacillin sodium salt View Scheme

dicloxacillin (3116-76-5) → methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide (10209-03-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaIO4 / or Dicloxacillin sodium salt View Scheme

dicloxacillin (3116-76-5) → Dicloxacillin S-sulphoxide methylester (83639-11-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaIO4 / or Dicloxacillin sodium salt View Scheme

Downstream Products

• 83639-11-6 Dicloxacillin S-sulphoxide methylester 
• 10209-03-7 methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide 
• 4888-90-8 phenoxymethylpenicillin sulfoxide 
• 36231-31-9 Dicloxacillin S-sulphoxide